Evaluation of the Mechanism of Heterogeneous Hydrogenation of alpha,beta-Unsaturated Carbonyl Compounds via Pairwise Hydrogen Addition | Sciact - CRIS-система Института катализа

Evaluation of the Mechanism of Heterogeneous Hydrogenation of alpha,beta-Unsaturated Carbonyl Compounds via Pairwise Hydrogen Addition Научная публикация

Журнал

ACS Catalysis
ISSN: 2155-5435

Вых. Данные

Год: 2014, Том: 4, Номер: 6, Страницы: 2022-2028 Страниц : 7 DOI: 10.1021/cs500426a

Ключевые слова

heterogeneous hydrogenation, pairwise hydrogen addition, parahydrogen-induced polarization (PHIP), reaction mechanism, α,β-unsaturated carbonyl compounds

Авторы

Salnikov Oleg G. ^1,2 , Kovtunov Kirill V. ^1,2 , Barskiy Danila A. ^1,2 , Khudorozhkov Alexander K. ^2,3 , Inozemtseva Elizaveta A. ^2,3 , Prosvirin Igor P. ³ , Bukhtiyarov Valery I. ^2,3 , Koptyug Igor V. ^1,2

Организации

1	International Tomography Center, SB RAS, 3A Institutskaya St., Novosibirsk 630090, Russia
2	Novosibirsk State University, 2 Pirogova St., Novosibirsk 630090, Russia
3	Boreskov Institute of Catalysis, SB RAS, 5 Acad. Lavrentiev Pr., Novosibirsk 630090, Russia

Информация о финансировании (7)

1	Российский фонд фундаментальных исследований	12-03-00403
2	Российский фонд фундаментальных исследований	14-03-00374
3	Российский фонд фундаментальных исследований	14-03-31239 (01201450183)
4	Президиум РАН	5.1.1
5	Совет по грантам Президента Российской Федерации	МК-4391.2013.3
6	Сибирское отделение Российской академии наук	60
7	Сибирское отделение Российской академии наук	61

Heterogeneous hydrogenation of α,β-unsaturated carbonyl compounds was addressed using the parahydrogen-induced polarization (PHIP) technique. PHIP effects were observed in hydrogenation of C═C bond of acrolein and crotonaldehyde over different supported metal catalysts, demonstrating the existence of a pairwise route of hydrogen addition to the substrate. Hydrogenation of acrolein over Pd–Sn/Al2O3, Pd–Sn/TiO2, Pd–Zn/TiO2, and Pd/TiO2 catalysts with parahydrogen also led to the polarization of the proton of CHO group of propanal. This was explained by C(O)–H bond dissociation which represents a side process on the catalyst surface. Formation of polarized cis- and trans-2-butenes was detected in hydrogenation of acrolein with parahydrogen over several Rh-based catalysts. This observation is made possible only due to the high NMR signal enhancement provided by PHIP. It was also found that hydrogenation of acetone and propanal with parahydrogen leads to polarized propane formation as a result of C–O bond hydrogenolysis.

Salnikov O.G. , Kovtunov K.V. , Barskiy D.A. , Khudorozhkov A.K. , Inozemtseva E.A. , Prosvirin I.P. , Bukhtiyarov V.I. , Koptyug I.V.
Evaluation of the Mechanism of Heterogeneous Hydrogenation of alpha,beta-Unsaturated Carbonyl Compounds via Pairwise Hydrogen Addition
ACS Catalysis. 2014. V.4. N6. P.2022-2028. DOI: 10.1021/cs500426a WOS Scopus РИНЦ CAPlusCA OpenAlex

Поступила в редакцию:	31 мар. 2014 г.
Принята к публикации:	13 мая 2014 г.
Опубликована online:	21 мая 2014 г.
Опубликована в печати:	6 июн. 2014 г.

Web of science:	WOS:000337074700043
Scopus:	2-s2.0-84902197018
РИНЦ:	24054751
Chemical Abstracts:	2014:802281
Chemical Abstracts (print):	160:708263
OpenAlex:	W2313630911

БД	Цитирований
Web of science	34
Scopus	36
РИНЦ	36
OpenAlex	36